Cooperative Rh(II)/Pd(0) Dual Catalysis for the Synthesis of Carbo- and Heterocyclic Compounds

Synthesis ◽  
2021 ◽  
Author(s):  
Kyu Ree Lee ◽  
Yu Lim Lee ◽  
Kyu In Choi ◽  
Sang-gi Lee
Keyword(s):  
Heterocyclic Compounds ◽  
Transition Metal Catalysis ◽  
Dipolar Cycloaddition ◽  
Reaction Parameters ◽  
Catalytic Systems ◽  
Metal Catalysis ◽  
Diverse Range ◽  
Judicious Choice ◽  
Dual Catalysis ◽  
Cyclic Compounds

Dual transition-metal catalysis has been introduced as a robust tool to synthesize a diverse range of organic compounds which are not able to be accessed by traditional single metal catalysis. In this context, we have recently developed the cooperative Rh(II)/Pd(0) dual catalytic systems, which have been utilized for the preparation of carbo- and heterocyclic compounds through the reaction between Rh(II)-carbenoid and π-allyl Pd(II)-complex intermediates in either synergistic or tandem relay catalysis. In synergistic Rh(II)/Pd(0) dual catalysis, the two reactive intermediates are generated simultaneously, which then undergo formal [6+3] dipolar cycloaddition to afford medium-sized N,O-heterocyclic compounds. On the other hand, tandem relay dual catalysis can be enabled through judicious choice of reaction parameters, which proceed through the insertion of Rh(II)-carbenoid into O–H or C–H bonds, followed by Pd(0)-catalyzed allylation to provide allylated benzofused cyclic compounds or chiral β-lactam derivatives.

1.2.1 General Principles of Transition-Metal/Photocatalyst Dual Catalysis

2020 ◽  
Author(s):  
J. C. Tellis
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Transition Metal Catalysis ◽  
Specific Role ◽  
Visible Light Photocatalysis ◽  
Metal Catalysis ◽  
Catalytic Transformations ◽  
Dual Catalysis

AbstractThe combination of transition-metal catalysis and visible-light photocatalysis offers opportunities for the development of unique new forms of reactivity. Presented in this chapter is an overview of the various strategies that can be used to design these dual catalytic transformations. Emphasis is placed on understanding the specific role that a photocatalyst can play in augmenting the reactivity of a substrate or cocatalyst to achieve otherwise challenging transformations.

1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

2021 ◽  
Author(s):  
Seema Thakur ◽  
Arunima Das ◽  
Tapas Das
Keyword(s):  
Natural Products ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Diverse Range

The 1,3-dipolar cycloaddition reaction of nitrone is one of the most important methods for the synthesis of different sizes of heterocycles which have enormous applications in natural products, biologically active molecules and pharmaceuticals.

Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1695-1706 ◽  
Author(s):  
Yongming Deng ◽  
Qing-Qing Cheng ◽  
Michael Doyle
Keyword(s):  
Transition Metal ◽  
Lewis Acids ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Membered Ring ◽  
Transition Metal Catalysts ◽  
Transition Metal Catalysis ◽  
Cycloaddition Reactions ◽  
Metal Catalysis ◽  
Phosphoric Acids

Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring heterocycles through asymmetric [3+3] cycloaddition are reported. Asymmetric organocatalysis uses chiral amines, thioureas, phosphoric acids, or NHC catalysis to achieve high enantiocontrol. Transition-metal catalysts used as chiral Lewis acids to activate a dipolar species is an alternative approach. The most recent advance, chiral transition-metal-catalyzed reactions of enoldiazo compounds, has contributed toward the versatile and highly selective synthesis of six-membered heterocyclic compounds.1 Introduction2 Asymmetric Formal [3+3]-Cycloaddition Reactions by Organo­catalysis2.1 By Amino-Catalysis2.2 By N-Heterocyclic Carbenes2.3 By Bifunctional Tertiary Amine-thioureas2.4 By Chiral Phosphoric Acids3 Asymmetric Formal [3+3]-Cycloaddition Reactions by Transition-Metal Catalysis3.1 Copper Catalysis3.2 Other Transition-Metal Catalysis4 Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazo Compounds4.1 Asymmetric [3+3]-Cycloaddition Reactions of Nitrones with Electrophilic Metallo-enolcarbene Intermediates4.2 Dearomatization in Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazoacetates4.3 Asymmetric Stepwise [3+3]-Cycloaddition Reaction of Enoldiazoacetates with Hydrazones5 Summary and Outlook

ChemInform Abstract: Dual Catalysis Sees the Light: Combining Photoredox with Organo-, Acid, and Transition-Metal Catalysis

ChemInform ◽  
2014 ◽  
Vol 45 (26) ◽  
pp. no-no
Author(s):  
Matthew N. Hopkinson ◽  
Basudev Sahoo ◽  
Jun-Long Li ◽  
Frank Glorius
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Dual Catalysis

Electrosynthesis of functionalized tetrahydrocarbazoles via sulfonylation triggered cyclization reaction of indole derivatives

2021 ◽  
Author(s):  
ZiZhen Yin ◽  
Yingjie Yu ◽  
Haibo Mei ◽  
Jianlin Han
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Transition Metal Catalysis ◽  
Cyclization Reaction ◽  
Indole Derivatives ◽  
Biological Chemistry ◽  
Metal Catalysis ◽  
Harsh Conditions

Synthesis of tetrahydrocarbazoles is of great interest due to its importance in organic and biological chemistry. Accessing such heterocyclic compounds usually needs harsh conditions or incorporation of transition-metal catalysis. Herein,...

C-H Bond Functionalization by Dual Catalysis: Merging of High-Valent Cobalt and Photoredox Catalysis

2021 ◽  
Author(s):  
Priyanka Chakraborty ◽  
Rajib Mandal ◽  
Soumen Paira ◽  
Basker Sundararaju
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Low Energy ◽  
The Other ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Dual Catalysis ◽  
High Valent ◽  
Energy Pathways

The merger of transition metal catalysis and photocatalysis has emerged as a versatile platform which opened the gateway to diverse low energy pathways for several synthetic transformations. On the other...

Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex

2016 ◽  
Vol 52 (49) ◽  
pp. 7699-7702 ◽  
Author(s):  
Liangliang Song ◽  
Lei Gong ◽  
Eric Meggers
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Rhodium Complex ◽  
Metal Catalysis ◽  
Precursor Complex ◽  
Dual Catalysis

A strategy for dual transition metal catalysis and organocatalysis is reported via disintegration of a single rhodium complex. Conveniently, the chiral-at-metal rhodium precatalyst can be synthesized in just two steps starting from rhodium trichloride without the need for any chromatography.

Dual Catalysis Sees the Light: Combining Photoredox with Organo-, Acid, and Transition-Metal Catalysis

2014 ◽  
Vol 20 (14) ◽  
pp. 3874-3886 ◽  
Author(s):  
Matthew N. Hopkinson ◽  
Basudev Sahoo ◽  
Jun-Long Li ◽  
Frank Glorius
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Dual Catalysis

Carbon‐Sulfur Bond Constructions: From Transition‐Metal Catalysis to Sustainable Catalysis

2021 ◽  
Author(s):  
Pratheepkumar Annamalai ◽  
Ke‐Chien Liu ◽  
Satpal Singh Badsara ◽  
Chin‐Fa Lee
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Sulfur Bond

An electrochemical perspective on the roles of ligands in the merger of transition-metal catalysis and electrochemistry

2020 ◽  
Author(s):  
Ke-Yin Ye ◽  
Jun-Song Zhong ◽  
Yi Yu ◽  
Zhaojiang Shi
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

The merger of transition-metal catalysis and electrochemistry has been emerging as a very versatile and robust synthetic tool in organic synthesis. Like in their non-electrochemical variants, ligands also play crucial...

Sign in / Sign up

Export Citation Format

Share Document